Matt MacInnis

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.

3 skills 4 insights

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Team & Organization Skills

Since the perfect number of resources is impossible to predict, it is safer to risk under-staffing than to allow the organizational rot and waste caused by over-staffing.

"When you staff a project, is it better to overstaff or is it better to under-staff knowing that you can't get it right? Well, it's better to under-staff. If you overstaff, you get everything that you..."
10:44

Withholding constructive feedback is not an act of kindness but a selfish choice to prioritize your own emotional comfort over another's growth.

"Fundamentally, the most selfish thing you can do is withhold feedback from someone. When you think a thought that would help someone improve and you avoid giving it to them because it would make you u..."
01:11:49

True top-tier success requires a culture that views comfort as a sign of failure and exhaustion as a byproduct of meaningful progress.

"If you want to be in the 99th percentile in terms of outcomes, it's going to be really difficult. You got to sort of remind people that if they ever find themselves in the comfort zone at work, they a..."
05:04

Leaders must proactively fight the natural dilution of intensity and the tendency of teams to prioritize their own comfort over company objectives.

"Teams will always optimize for local comfort over company outcomes. The purest form of ambition and most intense source of energy in the business is the founder CEO. Every next concentric circle of ma..."
01:00:58